


Waste My Time

by anniesardors



Category: Chicago PD (TV)
Genre: Established Relationship, F/M, Fluff and Humor, Truckstead talks
Language: English
Status: Completed
Published: 2021-02-16
Updated: 2021-02-16
Packaged: 2021-03-18 14:13:50
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,834
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29491134
Author URL: https://archiveofourown.org/users/anniesardors/pseuds/anniesardors
Summary: Missing scene from 8x06: A snippet of what happened between Jay and Hailey during those 6 hours in the truck
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 5
Kudos: 106





	Waste My Time

**Author's Note:**

> Thanks to the lovely anon on tumblr who requested this fic! This missing scene fic from 8x06 was such a fun one to write and I hope you all enjoy!

"So, how reliable is this CI?"

Jay rolls his eyes. "Hailey, it's been like a half hour. Something will happen. Just be patient."

She raises her eyebrow, challenging him because did he really just tell her to be patient. He just chuckles, settling further into his seat. They are sitting in the front seats of his truck, waiting for a deal one of his CIs said would go down. It was supposed to be a simple car exchange that would lead them to a drug deal, and Jay knows that waiting is a normal part of the process, but it is the part that Hailey hates the most.

"I don't do patient." She announces as if he has not been her partner for the past several years and witnessed firsthand how much she does not do patience.

"You waited actual years to tell me you had feelings for me." He can't help but tease her. "Seems pretty patient to me."

She scoffs, shaking her head. "I had to wait because someone kept almost getting himself killed."

"Next time don't have feelings for someone so reckless." He shrugs, glancing out the window. He is hopeful he will catch some action, but there is still nothing.

"Trust me, it wasn't planned."

It's true. None of this was planned. He thinks back to the first time he met her and can't help but smile because they have come quite a long way since then. He was so much younger then, and so much more broken. But now, he is older, wiser, and happier, and much of that is due to her.

"Do you remember the first time we did surveillance together?" Jay asks her. "Remember what you said?"

A smile curls on her lips at the memory. "That it wouldn't be my last time in the back of your van."

Jay chuckles. "I should have known then that you were going to ruin me."

Hailey rolls her eyes and is about to respond when Adam's voice breaks through on the two-way, asking if they see anything. Jay sighs, responding that he and Hailey still have not seen their guy.

"I remember when you first started," Jay murmurs softly after making sure his two-way is turned off. "You always did your hair all fancy."

She raises an eyebrow at him skeptically. "You saying my hair doesn't look good now?"

Jay shakes his head with a laugh, trying to figure out how to dig himself out of this hole. They potentially have several more hours in this truck and the last thing he needs to do is piss off Hailey within the first hour.

"Not what I'm saying." His response is quick. "I like your hair now. It's more...you."

"Yeah, well, I put a little more effort into my appearance the first few months because I was new and didn't want to lose my job." She explains. "Now, I just don't really care."

"Well," He says, leaning forward slightly, just enough that he can feel her heat, but not enough that anyone would think anything of their closeness. "I happen to think you look quite beautiful."

"If you're trying to sweet-talk me into making out with you in this truck, it's not going to work."

He falls back into his seat with a dramatic sigh that makes her giggle. He scans the area again, still not seeing anything remotely close to the deal his CI said would take place, before shooting her a wink.

"Got to pass the time somehow, right?"

Hailey just shakes her head before she tells him to keep dreaming and he tells her plans too.

They fall into a comfortable silence after that, both focused on watching for any sign of a potential deal. They comment on what they see and make a few jokes, but for the first hour or so, they are mostly professional. But, as time passes, it becomes evident that they will be in this truck for a long time.

It's not the place for long and deep conversations because they could be interrupted at any minute and she has already made it clear there will be no funny business in this truck, so he tells her a few updates on Will and his clinical trial. She listens intently and asks questions before turning the conversation to the latest updates in the Intelligence Unit. They talk about Kim and Mikayla and some things they want to do with the young girl. They talk about Vanessa and how much they miss her. They joke about how even after all these years, Platt still scares the hell out of them.

Eventually, the time bleeds away and before they know it, they have been sitting in the truck for close to four hours. Most of it has been spent in small talk or comfortable silence, but by the way Hailey is starting to drum her fingers against the window, he can tell she is losing her patience.

"I'm bored."

"Hailey, that is like the tenth time you have said that in the past half hour."

"Well, it's not my fault _someone's_ CI had their intel wrong."

Jay rolls his eyes, chuckling at her as he leans against the driver's side door of the truck so he can see her better. It was normal to wait around, especially when it came to info with CIs, but this was getting a little ridiculous. After one hour, Hailey was getting antsy. Now, she is practically squirming in her seat, needing some action.

It all makes Jay laugh, because she really is adorable when she is frustrated and bored, not that he would dare tell her that.

"I don't know what you want me to do." He says with a sigh.

"Entertain me." As a suggestive look grows on his face and he glances at the back seat, Hailey immediately regrets her words. "Not like that! We're at work."

"I didn't say anything!" He playfully argues, throwing up his hands for dramatic effect.

"You suck." She throws a wrapper at him from a granola bar she ate during their first hour of sitting in the truck. He raises his eyebrow at her choice of words, making her groan yet again. "I'm dating an actual child."

There is silence for a moment as their laughter dies out and he can still hear her drumming her fingers against the window. As he watches her from the corner of his eye, he can see her studying the area around them intently, as if manifesting in her mind that the deal will happen soon.

"Tell me a story." She says after a few moments, her eyes still peering out the front window. He shoots her a questioning glance as she shifts her in her seat to look at him better. 'We skipped that awkward normal part of dating where you ask each other their favorite movie and what you do for work. So, tell me something I don't know about Jay Halstead."

Maybe it's the delusion setting in from being stuck in this truck for over four hours that makes him not fight her, but more likely it's the fact that he knows she is right. By the time they were in a relationship, they already knew so much about each other. But still, despite their years of partnership and friendship, he knows there is still so much to learn.

"I played soccer in high school." It's not so much a story, rather a fact, but he does not think this is something he has shared with her yet, so he says it anyway. "I was offense, of course, because my coach knew I needed to be where the action was." He chuckles lightly at the memory of the one time his coach tried to get him to play defense in a game against their rival high school and quickly regretted it.

"Were you good?" Hailey asks softly.

"Wasn't bad. I mean I wasn't getting college scholarships or anything, but I was a starter on the varsity team."

"I never played sports." She tells him, playing with the zipper on her jacket while she talks. "I wanted to do soccer or track, but I worked at my parents' diner after school so I couldn't."

"What was that like?" She has mentioned a handful of times the diner, specifically the memory of the robbery where she met Platt that made her want to be a cop, but beyond that, he knows little of her time there.

If he's honest, he knows little about her childhood and he hopes that his question is not overstepping.

"It was a job." She says nonchalantly. "Working in food services...it builds character, let me tell you. Some people are really nice, but some people are just-"

"Jerks." He finishes her thought.

"Exactly. It was always better during the summers though, because they would normally hire one or two college students as summer help and I would have someone to hang out with besides my brothers."

"Oh, did Hailey Anne have a crush on a college boy?"

Her reaction is immediate, her body sitting up to lean against the center console to push him. He lets out a chuckle as she rolls her eyes.

"One guy."

"Well, now you have to tell me the details."

"Ugh." She groans dramatically. "Fine. It was the summer after my junior year. I think he was a sophomore in college maybe? His name was Derrik and he was the dishwasher."

Jay waits for her to add more to her story, a look of disappointment growing on his face when her lips purse close. "Come on, you can do better than that."

Hailey sighs, gazing back out the window as she finishes her story. "We used to take our lunch breaks together and he would tell me about how much fun college was. He was in a fraternity and everything."

"Wow." Jay teases. "So, you've always liked the bad boys."

The way Hailey's eyes roll, it looks like they are going to roll out of her head and he knows she probably is regretting asking him to swap stories.

"Ever go on a real date with him?" Jay asks.

"One." She tells him. "It was the movies and it was super awkward."

"Did he try to kiss you?"

"No...like I said, very awkward. But-" She pauses as she adjusts her position so her back is against the seat instead of the door. "Speaking of dates, when are you going to take me out?"

He glances over at her and sees a slightly teasing look, but he can tell by her eyes she is serious.

It's been three weeks since a kiss with her in a bar changed everything about his universe. After that night, they rarely spent a night apart. They went home together, went to sleep together, and woke up together. Weekends were lazily spent on her couch, watching a movie or taking a nap, and workdays were spent sneaking glances at each other and texting each other flirty messages.

But she was right. In the past three weeks, he had not taken her on a date.

He could blame the hecticness of the job or the chaos of the world, but he does not want to make excuses. Because Hailey deserves everything, and that includes a proper date.

"Okay, where do you want to go?"

She shoots him a surprised look. "Jay, I was just messing with you."

He knows she is trying to let him off the hook, but he doesn't want that. Because if the past three weeks are any indication, he very much wants to be on the hook when it comes to her. They've talked about this thing between them a few times and agreed they wanted to do what they needed to make it work-because this was it for both of them.

"Hailey," he tells her softly. "This isn't just some casual thing for me. I'm serious about us."

A small smile curls on her lips as she looks at him and whispers. "Me too."

"So, let me take you out on a real date."

"Okay," She says before her small smile turns into an all-out grin. "But, just so we are clear, I hate fancy dinners."

A hearty laugh escapes his body and he nods his head. "Got it. Although, I kinda already figured that."

"I'm serious. Don't be getting all fancy over this. I literally need you, some pizza, and a beer and I'll be set."

"Well, if that is how you define a date, we have been dating for like four years."

Hailey shakes her head with a chuckle. "Yes, but now you can kiss me afterward and I won't hit you."

He can't stop the smile that grows on his face because, yeah, now he can kiss her afterward, and it feels pretty damn good.

"Okay, so we are doing something better than pizza and a beer but not fancy tablecloths." He announces.

"You're going to overthink this, aren't you?"

His two-way crackles and once again Adam asks him if they see anything and once again the other officer groans when Jay reports that there is still nothing. Jay settles back against the car door and props up his elbow on the window, keeping his attention on both her and the scene in front of them.

"I just want to do this right." He says softly.

It takes her a few moments to respond. He is not sure if he caught her off guard or she is now the one who is overthinking things. She is gazing out the dashboard window so he can't see her eyes, but her face remains calm.

"I know." She says at last. "I want us to do this right too. But I honestly don't care where we go. I just want to be with you."

He wishes more than anything that they were not working because every fiber in his being wants to launch across the center console and kiss her. But, that response will have to wait until later. For now, he resigns himself to reach his hand across the truck to find hers, giving it a quick squeeze.

"You're amazing, you know that?"

"Yeah, I know." There's a pause before she turns over to him and flashes him a sweet smile. "You're pretty okay too."

"I'm not amazing?"

"You'd be more amazing if your CI didn't make us wait for four hours."

It's a typically Hailey response-joking, even during a sweet and sentimental moment. Her playful side is one he's only truly discovered since they got together, but it's a side of her that he does think he will ever get enough of.

"You keep complaining about that." He points out. "It's almost like you don't want to spend time with me."

"Eh," She shrugs. "Would have rather been paired with Kevin but-"

The words are lost on her lips when he loudly scoffs and crosses his arms, earning him a fit of giggles from the blonde detective.

"I'm kidding. You know you're the only person I could put up with for this long doing surveillance."

There is a hidden meaning to her words that they both hear. _You're the only person I would want to be with for this long. I like being with you._

"Good." He tells her a second later before adding. "You're the only person I want to do surveillance with too."

He likes being with her too.

She shoots him a pleased smile before turning her attention back to scanning the area in front of them. It is probably going on five hours now and he is sure that Hailey is going to complain several more times about being bored, but honestly, he does not mind. It is annoying sitting in this truck for so long just waiting, but he is with her, so there is nowhere else he would rather be.

"Just a hypothetical," He says after a few moments. "But what are the odds you'll make out with me in the truck after our date?"

That gets her laughing and he watches as that simply Hailey smile forms on her face.

"Play your cards right and I might even invite you back to my place." She says it flirtatiously as if they have not spent most of their nights together for the past few weeks.

"Noted."

As she scrunches her face happily and looks out the windows yet again, he finds it more and more difficult to focus on doing surveillance. Because, really, all he wants to do is watch her. He likes these moments with her, in the quiet of his truck, just being able to enjoy all that is Hailey. He likes the way she teases him and the little faces she makes and everything in between.

Part of him is secretly happy that his CI's information was wildly off. Because a couple of hours alone with Hailey? That's a day well spent.

**Author's Note:**

> Comments and Kudos are always appreciated!
> 
> Follow me on tumblr @anniesardors for more fics, to leave prompts, or to talk anything upstead!


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